First time anal sex and the bet

Putting force in my small hips my dick which was pointed at Nina's tight asshole, began to spread her hole open entering her backhole.

As I entered her amazing tight and convulsing hole, Nina's entire body tensed up, barring me from entering her furhter.

"I-it hurtsss," she moaned softly.

I smiled as her words meant it hurts, while the way she said it definitely meant she was feeling pleasure as well.

"Relax your body Nina, otherwise I can't go in further and I'll have to find another hole to accommodate my dick."

"N-no, I-I'll relax, j-just l-let me get used to it a bit," Nina said.

I smiled and raised my hand and made it flat.

*Pats pats*

I hit both her amazing ass cheeks with my hand, spanking her.

"H-huurrtss," Nina moaned.

She turned her head around and looked at me tear-eyed. I could instantly see though she felt good from it.

"D-don't hit me it hurts."

"Oh then why you moaning so hard when I hit you."

"T-there's no way that feels good," she said turning her head away from me again, embarrassed.

I enjoyed awakening her masochistic side. Seeing her so embarrassed not wanting to admit she was getting turned on from the pain.

"Relax your ass so I can enter it deeper or I'm going to continue spanking the bad slave."

"N-no don't spank me anymore, I-I'll relax."

Not long after I felt the tight hole loosen a bit and I immediately began entering her asshole deeper with me dick.

"Eeehhhhh," Nina moaned as I entered her ass as deep as I could, forcing my entire length inside her tight hole.

As my dick was fully inside her, I bent forward a bit and rested my hands on the bed next to both sides of her body as I said: "Prepare I'm going to start moving for real now."

I then pulled back before shoving it back in again.

"Aggguu, eeehh," Nina let out some sounds as I began going in and out her asshole.

"You're doing great," I said after a minute of moving.

'J-jusshtt, h-huurryy uppp. T-thisshh huurtsschh."

I smiled hearing the sweet pleasure filled voice. Yes was probably right in that it would hurt for her a bit, after all it was her first time anal.

But what she didn't voice out loud, was that she was definitely feeling good from it as well.

"As you wish I'll move even faster then."

She hurriedly turned her head around, with a shocked face. I met her nervous expression with a smile as I increased the pace of my dick entering her depths even more.

"Kuuhhh, n-nootttt goooood."

I realized what was happening soon.

"Don't tell me, you're going to cum from being fucked in the ass, by your little step-brother?"

"N-no way, w-whoo'd cumm from thissh."

"I see it's no good to lie to your master though. Now cum for me," I said increasing my pistoning even more.

"N-no pleasshe shtop. D-don't want to cum from this."

Giving her a few last hard thrusts, I came deep inside her rectum. I painted her entire inside white.

Meanwhile Nina began moaning loudly as well. Luckily the effects of the sleeping pills hadn't worn off yet, otherwise the house would probably have woken up by now.

"C-cumminnngg, I'm cumminnngg."

I let out everything deep inside Nina's intestines, filling her ass with a huge amount of semen.

After I finished I took my dick back out her asshole, looking at the entrance which I had forced wide open close up slowly again. The semen I forced deep inside being locked up by her closing sphincter.

I smiled and lied down next to Nina, who was still lying on her belly, breathing raggedly as she recovered from her orgasm.

I smiled listening to her mumbling.

"C-came, I came from anal sex."

I caressed her beautiful face which was covered in saliva and tears. "You did good, now let's do this everyday from now on."

"E-everyday? I-I'm gonna cum from anal everyday?" Nina said as she closed her eyes, falling asleep from the exhaustion.

I smiled looking at the beautiful sleeping girl. Loving the fact I owned her now and could start to have plenty of fun with her body.

I closed my eyes as well and drifted of immediately as I slept in the same bed as Nina.

The next day I woke up peacefully. Nina was still fast asleep. She had turned to her back in her sleep, which in turn showed my her amazing bare tits. I softly began groping her breasts as I said: "Wake up my dear sister, it's time for you to serve me once more."

Nina's face constricted as slowly her eyes opened. Smiling I said: "Good morning sleepyhead."

As she truly woke her eyes opened wide as she said: "I-it wasn't a dream?"

"Of course not, look at your belly if you want to see the truth."

Nina sat up straight and looked at her crotch, where the slave mark was fully in view.

"N-no," she said as she turned her head to me, "H-how could you do something like this to me?"

I chuckled and continued enjoying her firm breasts, "Because I wanted to do it, now give your master a good morning kiss."

"N-no, don't make me do lewd things with you anymore," Nina said as her head moved close to mine after which she pressed her juicy lips on top of mine.

Not long after I said while breaking up our lips for a bit, "not a little girl kiss like this. I want a hot French kiss with tongue."

"N-no Jake, please stop it."

But once again her body didn't listen to her as she opened her mouth a little before she put her soft lips on mine again, her tongue and mine entwining as we enjoyed hot deep intense kiss.

All the time my hand didn't leave her amazing breast, enjoying it greatly.

After a few minutes of having a deep sensual kiss I broke it and looked at her cute blushing face.

"So I guess this was your first kiss with tongue as well?"

"Y-you're cruel, y-you've taken all my first times and I have no choice but to resist."

I moved behind her as I grabbed both of her tits, enjoying groping them all the time while I said: "Why can't you just enjoy it. I've been making you feel good and cum plenty of times already right?"

"W-who's feeling good from this?"

"Just admit it Nina, you're a lewd girl who likes to be punished by me. As evidence you even came from having your first time anal sex last night."

"N-no don't make me remember that."

"Why not we'll be doing it plenty from now on anyway."

"N-no please don't put it in my butt anymore."

I sighed and said: "It seems you're really not liking this, so how about a bet?"

"Bet?" Nina said turning her head around as she looked at me.

"Yes if I win, you'll stop complaining and do your best to be the best sex slave."

Nina gulped hearing this but she once again took my bait, "A-and if I win?"

"I'll let you go, get rid of the slave mark and you can beat me up as much as you like."

"Oh you won't complain no matter how hard I hit you?"

"Nope, but that won't happen, after all you'll soon love your new role as my cute little sex pet."

"As if. Who'd enjoy being that. Now what's the content of the bet."

I smiled and said: "In one month's time I'll have you admit you love getting fucked in your butt."

"L-like hell I'll say that."

"Then you'll have no problem accepting the bet."

I stopped groping her tits from behind and moved in front of her, sticking out my hand I said: "If you shake it you'll accept the bet. If you don't then I guess you don't have any confidence in yourself."

Nina looked at me regaining some of her rowdy personality, "Hah like hell I'll lose to you. Just make sure you don't cry so much after I beat you.'

She then shook my hand. "Then it's a deal."

[Bet with Nina has been accepted.

Conditions: Make her admit to loving anal sex.

Time limit 1 month

If you win Nina will complain no more and her obedience will rise 15%.

If you fail, the slave mark will be removed and Nina won't be your forced slave anymore. She will also beat you up hard.]

I smiled seeing the system recognize the bet I made with Nina. Loving the fact her obedience would rise sharply as well. I wasn't at all concerned about her winning. After all I just had to make her admit it, while in fact she was already opening up to the pleasures of anal sex.

"Now that happened, stick out your butt towards me, in this month we're gonna have so much fun you'll have no way of winning."

"Hmpf, do your best I'll never admit it."

She obediently stuck out her butt towards me though. Smiling I pointed my dick at her ass' entrance once again, loving how easily she offered her asshole now.

"Just try and resist, in time though you'll love to be mine," I said as I pushed my hips forwards entering her amazing asshole once more.

"I-I'll never yield to you. aaahnnn," Nina already started moaning from a few thrusts and I was long from being done playing with her.

At the same time at my bedroom stood a surprised and more importantly a very horny woman.

"M-master's not here? B-but I want it. I want master's dick," Layla said as she squeezed her own huge soft breasts with one hand, while softly entering her pussy with her fingers."

She had once again sneaked away from her still sleeping husband to go and have sex with her master, but unlike the other time Jake was nowhere to be seen.